C3-Selective Trifluoromethylthiolation and Difluoromethylthiolation of Pyridines and Pyridine Drugs via Dihydropyridine Intermediates

Herein, we report a method for C3-selective C–H tri- and difluoromethylthiolation of pyridines. The method relies on borane-catalyzed pyridine hydroboration for generation of nucleophilic dihydropyridines; these intermediates react with trifluoromethylthio and difluoromethylthio electrophiles to for...

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Published inJournal of the American Chemical Society Vol. 144; no. 32; pp. 14463 - 14470
Main Authors Zhou, Xin-Yue, Zhang, Ming, Liu, Zhong, He, Jia-Hao, Wang, Xiao-Chen
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.08.2022
Amer Chemical Soc
Subjects
aromatization
Chemistry
Chemistry, Multidisciplinary
drugs
Lewis acids
Lewis bases
Physical Sciences
pyridines
Science & Technology
HETEROARENES
HYDROBORATION
ACTIVATION
FUNCTIONALIZATION REACTIONS
REDUCTION
ARENES
ARYL
C-H TRIFLUOROMETHYLATION
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Abstract Herein, we report a method for C3-selective C–H tri- and difluoromethylthiolation of pyridines. The method relies on borane-catalyzed pyridine hydroboration for generation of nucleophilic dihydropyridines; these intermediates react with trifluoromethylthio and difluoromethylthio electrophiles to form functionalized dihydropyridines, which then undergo oxidative aromatization. The method can be used for late-stage functionalization of pyridine drugs for the generation of new drug candidates.
AbstractList Herein, we report a method for C3-selective C-H tri- and difluoromethylthiolation of pyridines. The method relies on borane-catalyzed pyridine hydroboration for generation of nucleophilic dihydropyridines; these intermediates react with trifluoromethylthio and difluoromethylthio electrophiles to form functionalized dihydropyridines, which then undergo oxidative aromatization. The method can be used for late-stage functionalization of pyridine drugs for the generation of new drug candidates.Herein, we report a method for C3-selective C-H tri- and difluoromethylthiolation of pyridines. The method relies on borane-catalyzed pyridine hydroboration for generation of nucleophilic dihydropyridines; these intermediates react with trifluoromethylthio and difluoromethylthio electrophiles to form functionalized dihydropyridines, which then undergo oxidative aromatization. The method can be used for late-stage functionalization of pyridine drugs for the generation of new drug candidates.
Herein, we report a method for C3-selective C–H tri- and difluoromethylthiolation of pyridines. The method relies on borane-catalyzed pyridine hydroboration for generation of nucleophilic dihydropyridines; these intermediates react with trifluoromethylthio and difluoromethylthio electrophiles to form functionalized dihydropyridines, which then undergo oxidative aromatization. The method can be used for late-stage functionalization of pyridine drugs for the generation of new drug candidates.
Author He, Jia-Hao
Zhou, Xin-Yue
Wang, Xiao-Chen
Liu, Zhong
Zhang, Ming
AuthorAffiliation State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry
AuthorAffiliation_xml – name: State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry
Author_xml – sequence: 1
  givenname: Xin-Yue
  surname: Zhou
  fullname: Zhou, Xin-Yue
  organization: State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry
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  givenname: Ming
  surname: Zhang
  fullname: Zhang, Ming
  organization: State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry
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  givenname: Zhong
  surname: Liu
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  organization: State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry
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  givenname: Jia-Hao
  surname: He
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  organization: State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry
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  givenname: Xiao-Chen
  orcidid: 0000-0001-5863-0804
  surname: Wang
  fullname: Wang, Xiao-Chen
  email: xcwang@nankai.edu.cn
  organization: State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry
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Snippet Herein, we report a method for C3-selective C–H tri- and difluoromethylthiolation of pyridines. The method relies on borane-catalyzed pyridine hydroboration...
Herein, we report a method for C3-selective C-H tri- and difluoromethylthiolation of pyridines. The method relies on borane-catalyzed pyridine hydroboration...
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SubjectTerms aromatization
Chemistry
Chemistry, Multidisciplinary
drugs
Lewis acids
Lewis bases
Physical Sciences
pyridines
Science & Technology
Title C3-Selective Trifluoromethylthiolation and Difluoromethylthiolation of Pyridines and Pyridine Drugs via Dihydropyridine Intermediates
URI http://dx.doi.org/10.1021/jacs.2c06776
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